(2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol | 156925-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol
• 英文别名: (2R,3R,4S,5R,6R)-2-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 156925-78-9
• 化学式: C₄₀H₄₆O₈
• 分子量: 654.8
• InChiKey: PYEXQVIFSXOYAM-LBRCBTLPSA-N

物化性质

• 沸点：
  732.0±60.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-<(2-bromoethoxy)benzoxyphosphoryl>glycerol
  参考文献：
  名称：

  Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine

  摘要：

  The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol and (2R)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.

  DOI：

  10.1021/jo00128a043
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-glucopyranoside 、 (S)-2,3-O-isopropylideneglycerol triflate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2,3-O-isopropylideneglycerol 、 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-2,3-O-isopropylideneglycerol
  参考文献：
  名称：

  Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine

  摘要：

  The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol and (2R)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.

  DOI：

  10.1021/jo00128a043

文献信息

• Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine
  作者：Donald E. Bierer、Larisa G. Dubenko、Joane Litvak、R. Eric Gerber、Judy Chu、Dung L. Thai、Michael S. Tempesta、Thien V. Truong

  DOI：10.1021/jo00128a043

  日期：1995.11

  The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol and (2R)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.